


Traditional and Non-Traditional Entries

by Khashana



Series: Advertise what makes you crazy (The Olympic Figure Skating AU) [3]
Category: Check Please! (Webcomic)
Genre: Anal Sex, Doggy Style, Double Penetration, Dysphoria, Internalized Transphobia, M/M, POV First Person, Period Sex, Periods, Strap-Ons, Trans Male Character, Vaginal Sex, blood mentions, but don’t worry I’m trans so I’m not gross about it, nonlinear timeline, porn without plot/plot what plot, transgender character
Language: English
Status: Completed
Published: 2020-06-11
Updated: 2020-06-11
Packaged: 2021-03-04 01:15:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,799
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24655183
Author URL: https://archiveofourown.org/users/Khashana/pseuds/Khashana
Summary: Or, five times Kent gets fucked and one time he doesn't.
Relationships: Eric "Bitty" Bittle/Kent "Parse" Parson, Eric "Bitty" Bittle/Kent "Parse" Parson/Jack Zimmermann, Kent "Parse" Parson/Jack Zimmermann
Series: Advertise what makes you crazy (The Olympic Figure Skating AU) [3]
Series URL: https://archiveofourown.org/series/1754023
Comments: 7
Kudos: 64





	Traditional and Non-Traditional Entries

**Author's Note:**

> Title from a terrible figure skating pun thanks to MaraMcGregor. Pure unrepentant porn. Enjoy!  
> (also please notify me if you find continuity or SPAG errors, especially tense changes. there was more than the usual amount of trouble with this one.)

**Prologue**

“I’m gonna skate for _me_ now,” I say.

He’s looking at me like he wants to…kiss me? Eat me? Look at me forever?

That place inside me is throbbing. Wanting.

I kiss him, and he kisses me back, hungry for it, and the place throbs harder.

I want him.

But we get back to my room, and it’s wrong, wrong, wrong. Something curdles inside me to hear him call me beautiful.

The truth bursts out of me with an inevitability.

Somehow, he’s fine with it.

**February 2009: The first time**

I want him inside me. Guilt prickles at the back of my mind, telling me I can’t be a boy if I want it like this. But god help me, I do.

I climb back into his lap and hook my ankles around his back, pulling myself in and guiding him to my entrance with one hand. It burns, so I pause to run my hands up his chest, cup his face, willing myself to relax. I have Jack’s dick ready and waiting for me, and _want_ shoots through me at the thought. I pull him a little deeper, using my heels behind his back for traction, but the burn spikes, and I pause again, frustrated. He pulls my face a little closer to kiss me, and we stop to make out a little, open-mouthed and eager. The place inside me screams to be filled, and I pull a little more. It doesn’t burn so much now, more like a slightly uncomfortable pressure, which I can deal with. I inch closer, and closer, and then my hips meet his, and I’m sitting in this gorgeous boy’s lap with his dick inside me. I reach up to kiss him again, needing a minute, and this time I slide my tongue alongside his, which feels better than it has any right to. He twists sideways to press his mouth closer, kiss me deeper, one hand cupping the back of my head and the other still clutching my hip. The pain is really fading now, and I’m getting wetter by the minute. I shift in a tiny thrust, back and forth, and he slides ever so slightly out of me, and back in.

He starts to lie back, but I tell him, “No, like this,” and pull his arms to wrap around me.

His dick presses into me in all the right places, the tip rubbing that spot near the top of my vagina. I squeeze my internal muscles without meaning to and the sensation doubles, a hundred happy nerves pressing into something solid, the mouth delighting at the stretch. I like this position. We aren’t really fucking so much as pulsing, _grinding._ One of his hands creeps down to grab a handful of my ass, and oh, _yes,_ I liked being in control but I like the illusion that he’s pulling me down onto his dick just as much.

“Fuck,” I mutter, and the other hand joins the first, pulling me down onto him harder, and I’m split open, and it’s wonderful.

“Flip me over,” I whisper.

He does, but doesn’t start to fuck me, just plants his knees and continues to grind into me at that wonderful angle. I keep my heels tucked behind his back and press up into him, over and over in short strokes. I’m surprised by how much I like him covering me like this. I feel safe. Even from underneath, I take my pleasure from him, thrusting up and grinding into him, pressing into my clit as he thrusts down into me. I’m trying to make it good for him, too, clenching down rhythmically, and he seems to enjoy that, from the panting in my ear.

The sensation in the walls of my vagina is starting to fade as the slide gets easier and easier, but I hardly notice because that spot at the top is screaming for more, for him to pound it harder, and every time he hits it sparks fly down my nerves.

“Harder,” I tell him. He pulls back just a little more, just enough to work up more force when he pushes in, and I’m at the height of my pleasure now, body singing, and this isn’t going to last much longer. “I’m close,” I tell him, and direct his thrusts with my legs so he hits at exactly…the right… _pace._

I read once that the female orgasm lasts for seven seconds at the most. Even putting aside the cissexism, I know that isn’t true, I’ve timed it on my watch before when I was particularly horny and bored, and I’ve gotten at least twice that. I pull him in roughly with my heels and hands, ensuring he stays still and doesn’t try to fuck me through it as my muscles seize, my breathing stops, and pleasure floods my body.

I don’t moan when I come, generally speaking. You can get off a lot more often if you don’t have to worry about being overheard, and it usually hurts my throat, besides. I pant a little instead before I run out of air and just hold him there, floating in bliss before it fades and I let myself relax and inhale.

“You can fuck me now,” I whisper, because I’m not sensitive inside, just swollen from the orgasm, and he does, pulling almost all the way out to thrust back in a handful of times before shuddering himself to completion.

I’ve had penetrative sex, with a boy who knows _I’m_ a boy, and the world didn’t end.

That seems like a good sign.

**April 2009: Period sex**

There’s an ache deep in my stomach that I recognize from long years of experience, and it fills me with revulsion and misery. I’m already sitting on my bed, so I wrestle the covers out from underneath myself and burrow under them. The heat dulls the ache to something barely noticeable, and the blanket hides my breasts and hips from view.

But now, of course, if I want Advil, I have to get out from my cocoon. I waver about it for a good twenty minutes before I’m saved from my dilemma by a knock on the door.

“Come in,” I call.

It’s Jack. Obviously. It’s his house, after all

“You didn’t come down for breakfast,” he says, brow furrowed.

“Cramps,” I say shortly. “Can you bring me some Advil?”

He brings me the Advil, a glass of water, and a Pop-Tart on a plate. I might love this man. I take the Advil and consume the Pop-Tart in about five bites, Jack sitting next to me on the bed, waiting patiently. I kiss him in thanks. He takes the plate away, sets it on the floor, and kisses me back, and it turns into lazy making out, and then less lazy making out. He starts to peel the covers off of me, and I snatch them back. He breaks off to frown at me. I summon my best glare for him.

“You…don’t want to hook up?” he tries.

“I don’t want to come out from under my blanket,” I correct, feeling brittle. If he asks me why, I’m probably going to throw him out. On a regular day, I could just say it, just explain how this makes me feel and how it’s better if I can’t see myself, but right now, it’s far too close to the surface.

He doesn’t ask. He makes several faces at me, and then says, “Can I come under with you, then?”

Startled, I nod. He stands up and strips out of his jeans, leaving him in boxers and a T-shirt, and then lifts the edge of my blanket to slip underneath. We’re lying on our sides, facing each other, about six inches apart, and we just stare at each other for a few seconds. Then he scoots closer, oh-so-carefully, and pulls me into another kiss.

We make out for a long time, inching closer by intervals until our legs are tangled and our hands are roaming under the blankets, shoving up shirts to stroke flesh, grabbing butts, cupping faces, winding through hair. He’s hard now; I can feel him through our underwear, grinding against me. I hook one leg over his hip so his dick rubs right up between my legs and we break the kiss simultaneously to pant.

“Do you—want to just—get off like this?” he gasps.

I consider it. It feels really good, just like this, and I know if I angle it a bit better I can get off. But…

“Nah, I want to fuck,” I answer honestly. “Just like this?”

He nods, and we break apart. I shimmy out of my underwear and he roots in my bedside table for a condom and tears it open. I hear him pop open the button of his boxers and roll the condom on. There’s something oddly exciting about how neither of us can see him doing it, like our sex is a sweet secret from the whole world. We roll back to our original positions, my leg hooked over his hip and his erection rubbing up against my wetness, but this time I reach down, grasp his cock, and guide it home.

Jack’s boxers are bunched around his thighs; I can feel them with my foot. But I can’t _see_ them, no one can see what’s happening here. We’re under the blanket almost up to our shoulders, shirts still on, we could just be making out here. We’ve never had sex under the blankets like this. I get overheated too easily and I usually like to be able to see what I’m doing. Maybe that’s why it seems like a novelty. And it _is_ too hot; I kick the blankets away enough for my feet to get some air, which is a relief.

I pull him into me, over and over, digging my heel into his back, and he meets me halfway at every thrust. His big hand cups my face and he kisses me breathlessly.

It doesn’t take long, like this, not once Jack slips a hand down between us and starts touching me, thumb making hard, fast little circles right where I need him.

“I’m close,” I tell him, as I always do, so that he can do exactly this: When I get there, he grabs my ass to hold me still and _slams_ in, holding himself fully sheathed so I can clench down on him and wring extra, long, precious seconds out of my orgasm and flood my body with oxytocin. Today, it has the wonderful side effect of killing my cramps instantly.

When I finally relax, still riding lovely aftershocks, he picks up again, and he fucks me faster and faster until he hits his own peak and shudders in my arms.

He pulls out, but I stop him from taking the condom off and do it myself. He gives me a quizzical look, which sharpens into understanding when I hold it up, hands and condom streaked with blood.

Still, he protests, “I could have done it. I’m not squeamish.”

“I’mma hit you with the bloodborne pathogens binder you _surely_ had in high school chem.”

“But…” I ignore him, standing up to dispose of it and wash my hands.

“It’s _my_ blood, Zimmermann, quit making this _weird._ ”

**January 2012: In the back door**

“Hey, I was thinking,” says Jack one day. “You know how you were saying that even though you love, um, the sex we have, that you have to fight through the internalized-transphobia voice in your head that says you shouldn’t like it like that?” He’s blushing by now, eyes firmly fixed on the wall.

“Yeah.” I have said this, on a couple of occasions.

“Well. Would you ever want to try. Um. Anal?” He’s absolutely scarlet now, I note somewhere in the back of my head, but most of my brain is taken up with evaluating the proposition.

My first thought is _wouldn’t that hurt_ , but cis gay guys do this all the time, right?

“You’ve done the research?” I say instead, because of course Jack has, that’s what Jack does.

Predictably, he nods, still staring at the wall.

“Yeah, all right,” I say, surprising both myself and Jack, if his expression is anything to go by. “Send me what I need to read.”

I do my reading, acquire some gloves and lube, and experiment. The websites are right that it’s weird to stick something in my ass; all my instincts are telling me to push my fingers back out again. It isn’t sexy, at first. But then I try jerking off, sneaking up on myself in the middle of it, and oh yeah, I could get used to this. As long as I remember to _relax_.

“Hey,” I ask Jack on a particularly horny Saturday afternoon, “remember the thing you suggested?”

“Which thing,” says Jack absentmindedly, poring over his math homework.

“The thing where you take me in the back door instead of the front.” It’s my turn to blush, but at least Jack’s right there with me, homework completely forgotten.

“Yeah?”

“What do you think about trying that in, like, half an hour?”

“Why half an hour?”

“Let me get ready.”

“Oh. Yeah. Sounds good.” He’s wearing the expression that means his mind’s just been blown by lust. I throw him a smirk and dash off to the bathroom, where I’ve hidden a douche kit for this purpose exactly. The head start also lets me start working a finger into myself without an audience. This part is almost familiar by now. I get myself off once, quick and perfunctory, just to relax and ease the way.

When Jack walks in, he actually grabs for the doorframe as though to steady himself. “Calisse, Kenny, you should see yourself.”

“Come here,” I tell him, and turn over onto my hands and knees. Soft rustles and thumps tell me Jack is stripping behind me, fast like he’s preparing to play hockey, and then picking up the lube lying on the bed and squirting some into his hand.

He starts off with fingers, and that isn’t too weird. I’ve gotten as far as three before, though at that point the contortion required had gotten weird. Now, Jack slips in one finger easily, works it around for a few seconds, then adds a second. That takes a little longer to adjust to, but not too much, and then three. I press the heel of my palm to my dick, and okay, now things feel like _sex_.

Jack withdraws his hand.

“You ready?”

“Yeah.”

“Uh. Do you care if I wear a condom?”

“You haven’t slept with anyone besides me in the last year and a half, have you?”

“No!”

“And you can’t get me pregnant like this, right?”

“...Right.”

“So go for it.” Vaginas aren’t exactly sensitive enough to tell the difference. My ass might be, though.

The sound of more lube being squirted into a hand. The tip of Jack’s dick brushes against my asscheek, and then my hole. A breath, and then he _pushes_.

I breathe out and concentrate on not fighting it. Familiar hands grip my hips, pulling them flush ever so slowly. He slows down to almost nothing as his dick stretches where his fingers couldn’t reach and I inhale sharply. _Relax,_ I tell myself.

And then he’s all the way in, pressed along the backs of my legs. A beat, then he drops a kiss onto my back. And then he starts to move.

His hands slowly curl around to my stomach and inner thigh, maybe on purpose or maybe not, pulling me close in a way that makes it obvious we’ve been together just short of forever.

Pleasure ricochets through my body as Jack thrusts deep inside, hand on my thigh reaching forward to press against my dick, cradling me against him in a way that’s both sexual and somehow tender. And then all I can do is gasp and pant and let Jack take me up, up, up, and over the edge.

He tries to keep fucking me as I come down, limbs sparking with the force of the orgasm, but it’s way too sensitive all of a sudden, and I hiss.

“You want me to pull out?”

“Yeah.”

He lies beside me and strips off the condom, and I reach for him to jerk him off, feeling smug when he comes only a few moments later. I snag a tissue from the bedside table and wipe off my hand, then ball it up and toss it to the trash. We lie there for a few breaths.

“Thanks,” I say quietly.

“’Course,” Jack says, just as quietly.

That’s more than enough feelings for one conversation already, but I can’t bring myself to ruin the mood, so I just curl into his side and we sleep.

**October 2014: Bitty**

Jack’s off at class thing the first time Bitty and I do it alone. We’re watching a movie, or Bitty’s watching a movie and I’m staring at the soft skin of his neck, indulging in a choice fantasy. When he tilts his head unconsciously sideways, I decide I have no actual reason to exert self-control, and tug him closer to press a wet kiss to it. He hums happily, and, pleased that he seems receptive, I unbuckle his jeans blind.

Bits breaks away to gasp, “Just us? We’ve never…”

“Do you not want to have sex just with me?”

“No, I do, I just wasn’t sure if this fit the terms of your…” He waves a hand. “Agreement. With Jack.”

“Oh. We never laid it out that explicitly, but I got no reason to believe he’d have a problem with it. You want me to call him?”

“N-no. Not if you think he’d be fine.” But Bitty sounds hesitant, so I pull out my phone and text him.

_Yo do you mind if I sleep with Bits_

_Not as long as you tell me about it later_

“Green light,” I report. “As long as I bring deets.”

“You, um, really want to?”

“Bits,” I say seriously. “I am actually dying to get your dick in me right now. That cool?”

He laughs, flush high on his cheeks, and nods. I finish pulling his dick out of his pants and give it a few sharp tugs before dashing to the bedroom for a condom, stripping off my shirt as I run and pausing to struggle out of my jeans. When I turn around, I almost bump into him, also naked by now.

“Oh. Hello.”

“Did you not want…” He gestures. “Bed?”

I sigh theatrically. “I _guess,_ given the opportunity, we should probably fuck on the bed instead of the sofa. Since we’re _here_ and all.” I rip open the condom and roll it on him as he laughs, then nudge him toward the bed. He sits down, and I make him scoot back toward the headboard. Then, I take his dick in one hand, liberally apply the lube, and just fucking sit down on it, forcibly relaxing and already loose from arousal. He gasps, one sound that turns into something more like hyperventilation as I ride him, fast and furious. His dick is smaller than Jack’s, which means I can arch my back and it hits my G-spot perfectly. I rub at my own dick and, oh, this isn’t going to last very long. I come in about a minute, harder than I expect from a quick-and-dirty like that, clamping down on Bitty’s dick and riding every inch of pleasure I can get out of it. He moans, presumably because I have his dick in a vise, but doesn’t come.

I lean back on my hands and catch my breath for a minute.

“Woo. That was good.” I catch sight of his expression and add, “Don’t worry, we’re not done. I just need a few.” It was a good enough orgasm to actually warrant a real refractory period. I just breathe for a while, clenching down every so often just to make sure he stays hard.

By the time I’m ready again, he can’t keep the frustration off his face, and I try not to laugh at him. I ride him to a second orgasm, then flip over to my hands and knees.

“Really?” he gasps, winded.

“Go for it,” I agree, just as breathless. He guides himself back in, then grips my hips with both knees and goes to _town._ The bed shakes, so I don’t have the balance to pick up one hand and jerk off, and Bitty’s getting me right in the best spot, but I _cannot_ come untouched. I’ve had two already, so I let him drive toward his own finish despite the frustration, but then he reaches around and grabs my dick. I groan in surprise and pleasure, and abruptly I’m almost there.

“Tell me how you like it,” he pants in my ear, so I tell him how to touch me between gasping breaths. He’s starting to jerk out of rhythm; he’s close, and I plead to my own dick to finish a third time before he tenses up too much and ruins the orgasm. But he surprises me by grunting and shuddering to completion deep inside me without stilling his hand; haphazard as the rhythm is now, it’s enough. I think _Bitty just came in me_ and seize up, red-hot pleasure shooting through my whole body, and he comes back to himself in time to regain his former pace and drag the pleasure out. 

_Bitty got me off three times_ I text Jack smugly, with three eggplant emojis.

_Crisse it’s THAT kind of night is it_

I snicker.

_I don’t know what you’re talking about_

_Yeah yeah you’ll be ready for another round when I get back_

I can’t even argue.

**February 2015: DP**

It starts off as a joke. I’m riding Jack, Bitty pressed up against my back, dick rubbing against my ass and teeth buried in my neck.

“You like that, huh, Bits?” I pant. “Wishing you could just slip inside?”

Bitty _freezes._ So does Jack.

“Well, now that you mention it,” says Bitty breathlessly.

“Would you want that, Kenny?” says Jack.

I think about it. “Yeah, actually. I do.”

We don’t do it that day. We _plan_ this fucker, and I don’t know when we started actually scheduling sex, but I can’t disagree with the results. I make sure I’m ready in enough time. Jack and Bitty and I negotiate who’s in front and who’s in back, and all agree to let Bitty in back, because he’s never actually tried that before. Jack sucks me off, quick and dirty, a means to an end. This will be easier if I’m more relaxed.

So it isn’t the same night, but I have déjà vu anyway, because it’s looking like the same position. I’m perched over Jack’s lap while he slips lubed fingers inside my front hole. As soon as he’s done, Bitty’s doing the same to my back hole. Already it’s intense, and they’re not even doing it at the same time.

“Am I doing this right?” Bitty asks nervously.

“Perfect, babe,” I assure him. When they’re both satisfied, I get off Jack’s lap so they can finish undressing, and Jack leans back on the bed, butt scooted right up to the edge so Bitty will have some traction. I plant my hands on his shoulders, and he helps aim. I sink down astride him, inch by inch—I’m loose from the earlier orgasm, but still swollen for the same reason.

When I’m seated, I breathe for a minute, and then rise up on my knees and set back down, letting his length slide in and out of me, getting used to the sensation. God, he feels good, every time the head catches on my opening. I could just ride him to completion, but that isn’t what we’re here for.

“Ready for you, Bits,” I say, and feel Bitty’s hands on my shoulders, my sides, my hips. And then he’s pushing into me.

It’s not, of course, an unfamiliar sensation. Except for how it’s brand new, because I’m already stuffed full of cock and Bitty has to move agonizingly slowly. We’re all letting out little bitten-off moans. I’m not usually loud, but this is so incredibly intense. I think I can feel Bitty’s dick pressing up against Jack’s through my inner walls, filling me impossibly fuller, fuller. Finally, he’s seated. He pauses for a moment, giving us all a chance to get used to it, and then he starts to move. He pulls out, slowly, so slowly, and shoves back in, a little faster, and again, and again. I try to rise up on my knees, ride Jack, but it throws us off rhythm almost immediately, and Bitty slips out.

“Here, let me try something,” says Jack. “Bitty, if I scoot back a little, can you still reach?” They maneuver so Jack has his feet up on the bed, heels pressed tight against the backs of his thighs. He has me straddling him, practically doing the splits because his legs are in the way, but that’s okay. I’m flexible. It takes Bitty a little more maneuvering, but he manages to slip back inside. I brace myself against Jack’s chest, and they start to move again, slowly, slowly, Jack thrusting _up_ and Bitty thrusting _in_ , mostly in sync because they figure out pretty quickly that it won’t work any other way.

I’m so full, so incredibly stretched, more turned on than I know what to do with. I’m shaking too hard to hold myself up now, so Jack puts his feet back on the floor and sits up unaided. My vision blurs and I blink tears away, surprised and yet not. They have to stop moving almost entirely to pull it off, but they bracket me in a hug, the most obscene cuddle I’ve ever been part of. And then, oh god, Jack puts his hands on my hips and lifts me. I knew he could pick me up, okay, we do that literally all the time, but he doesn’t do it here, not when I’m on top, he doesn’t lift me and fuck me down onto his cock, because when I’m on top I want to be _on top,_ but I don’t have the leverage to do it now, and so Jack does it for me. They can’t get all the way out, either of them, so it’s just little strokes, but that’s my favorite kind anyway. Together they’re hitting me in all the best places. Jack’s hands are busy, but Bitty’s aren’t, and one of them snakes around to touch my dick. And that, that’s game over.

“There,” I tell them, “there, there. Yeah. Don’t stop. Close.” They don’t stop. They fuck me, and jerk me off, and hold me, and _fuck_ me. My orgasm builds and builds, way higher than it usually gets without me tipping over the edge, I don’t know what the difference is, but they push me higher, and higher, and then I’m coming. Bitty moans long and loud behind me, and I know I’ve pushed him over too.

Jack lifts me off them both, carefully, oh so carefully. He lays me down beside him on the bed. Bitty heads for the bathroom, and Jack yanks off the condom and jerks himself off roughly. Ten or so strokes, and then he’s coming, face screwed up beautifully. I can barely move, but I appreciate the view.

Bitty comes back with a warm washcloth. He wipes me down carefully, then passes it to Jack to wipe off the jizz on his belly almost as an afterthought. Jack helps me sit up, and Bitty cracks the cap of an orange juice and passes it to me. My hands are shaking, but I brace my elbow against Jack and manage. I laughed at them when they brought this up originally, but now I’m glad of the aftercare. I drink the orange juice as fast as I can, still breathing heavily, eager to lie back down.

“Sleep, Kenny,” Jack says when I manage it. Bitty curls up on my other side. “Sleep.”

**May 2013: Kent's turn**

“Hey,” says Jack one day, too casually. “Would you ever be interested in, ah, topping?”

“Like, with a strap-on?” I say, as though this is a perfectly normal thing to say when we’re both doing our homework.

“Yeah.”

“I would be very down for that.”

“Yeah?” He’s blushing, unsurprisingly.

“If you think I would pass up the opportunity to get inside that bubble butt, you’re kidding yourself.”

“I—uh. Okay. I’ll just buy one then, shall I?”

“Don’t buy it online,” I say. “We’ll go into the city.”

He stares at me. “You want to walk into a sex shop and interact with a live human cashier who knows you’re buying a dildo.”

“Well, when you put it like _that,_ it doesn’t sound like fun,” I complain. “But if we buy it in person, we don’t have to pay rush shipping or wait a month, and we’ll have it for the kegster weekend after next.”

“Why is that important?”

I level him with a look. “Jack. I cannot stress enough how much, inexplicable though it may be, kegsters get me in the mood to fuck you.”

So we buy the strap-on, and Jack disappears into his room to review all of my research, and he leaves to “get ready” for the kegster a good two hours before it starts. This strikes me as amusing, but I don’t say anything, for fear of damaging my chances of getting laid tonight.

I watch my drinking more carefully than usual. I want coordination for this. Otherwise, the kegster begins the same as usual. I dance, with Holster and Lardo and some soccer team bro, and Jack wanders the room and does his requisite socializing.

Until he doesn’t.

Until he finds me on the dancefloor and uses those hockey muscles to hold himself at the same height as me, and grinds his ass inexpertly against my crotch. My hands are on him even as I gasp, sliding up under his shirt and then coming down to his hips to bring him into sync with me.

I’ve never bothered to spend the money on a soft packer. On the rare occasion I get that kind of dysphoria, a ball of socks and some safety pins does quite nicely in a pinch. I’m doing just that today, but this time, it isn’t dysphoria, it’s for this exact reason.

Jack gasps a little, probably not expecting the bulge in my pants to press back against his ass. I bite his neck, and the gasp turns into a moan.

“Oh my god, Kenny.”

Unable to resist, I run a hand down the front of his pants. He’s not hard yet, but I’m confident I can change that. I pull away, dart around to his front, and resume grinding, only now we’re crotch to crotch. I kiss him, and he kisses me back desperately, groaning into my mouth when I grab two handfuls of his ass and squeeze.

“Get it, Kent!” It’s Shitty yelling at us, and I have to pull away to laugh.

“Wanna?” Jack’s voice is horny levels of deep and I needed to fuck him _yesterday._

I grab him by the hand and we make for the stairs.

Jack pulls off his t-shirt while I unbutton his jeans and pull the zip. Then it’s my turn to undo my shirt buttons while he takes my pants and my snapback off. We shove our own underwear (ball of socks and all) to our ankles, and then we’re back on each other, kissing, hands wandering. I grab his ass again, pulling him close to grind up against me, and it feels better naked, of course it does.

He breaks away to open the closet and pull the box down, handing it to me. I unwrap it.

I saw it before, of course, in the store and after we got it home, but it’s different now, knowing it’s time to use it. I step into the harness and hold my hand out for lube, which Jack squirts into my palm without being asked. I lube up the part that goes inside me and slide it in carefully. It’s really only about the size of a bullet vibe, just enough to satisfy the need. I tighten the fastenings and stroke the dick, smearing the rest of the lube over it.

Jack’s still standing there dumbly, watching me, so I come over and kiss him, only when I touch his ass this time, I slide all the way back and probe at his hole. One finger slides in pretty easily; he’s already lubed up. I can’t get very far, though, not with this angle, so I walk him back toward the bed and get him to lie back. I kneel on the bed, and he swings a leg up over my shoulder. I stick two fingers in. The rush is amazing.

I work Jack slowly up to three fingers, then four. He’s writhing on the bed, covered in sweat, moaning my name and making me glad for the eardrum-bursting music downstairs.

“Do you wanna flip over?”

“No,” he pants. “Like this.” He grabs a pillow and slides it under his own hips, and I position myself over him.

The anticipation is almost as good as sex in and of itself.

Jack wraps a hand around the base of my silicone dick and presses the tip inside himself. I push slowly, watching his face. I’m remembering what it’s like for me, and using that, and he’s clearly doing the same, and we’re so utterly in sync as I bury myself in Jack Zimmermann’s legendary ass.

We breathe together for a moment, and then I feel him relax, and I start to thrust.

I experiment for a while, trying speeds and angles and force, and when I find the one that makes him wail, I go to town, fucking into him over and over and apparently nailing his prostate.

I’m shaking too much to balance on one hand and jerk him off, and maybe he gets that, because he reaches up and does it himself, timing his strokes with my thrusts. Together we get faster, until he’s jerking it faster than I can fuck, and then he screws up his face and comes on his stomach and his bedspread, groaning my name.

I switch angles, not pulling out completely, but just a few short, sharp pulses with the strap-on rubbing against my actual dick _just right_ , and I come buried deep inside him with a shout.

“ _Jack!_ ”


End file.
